Bh. Wang et al., CHEMICAL FEASIBILITY STUDIES OF A POTENTIAL COUMARIN-BASED PRODRUG SYSTEM, Bioorganic & medicinal chemistry letters, 6(8), 1996, pp. 945-950
By using model amines, several amides of coumarinic acid with the phen
olic hydroxyl group protected as an ester were prepared. These model a
mides underwent a facile (t(1/2) 1.5-31 min) lactonization to release
the original amine compounds upon esterase catalyzed hydrolysis of the
phenolic ester. Such a system can be used for the preparation of este
rase-sensitive prodrugs of amine-containing compounds or peptides. Cop
yright (C) 1996 Elsevier Science Ltd